Aldicarb sulfone

HCID 15438

Basic information

CAS
1646-88-4
Standard SMILES
CNC(=O)ON=CC(C)(C)S(C)(=O)=O
InChIKey
YRRKLBAKDXSTNC-UHFFFAOYSA-N
Molecular formula
C7H14N2O4S
Average molar mass
222.26 g/mol
Monoisotopic mass
222.06742793

Overview

Aldicarb sulfone is a white crystalline solid. Insecticide.

Names & identifiers

Preferred name
Aldicarb sulfone
IUPAC
[(2-methyl-2-methylsulfonylpropylidene)amino] N-methylcarbamate
English name
Aldicarb-sulfone
Molecular formula
C7H14N2O4S
Molecular weight
222.26

Names & synonyms

DTXSID6023862RefChem:915377DTXCID308098061646-88-4Aldicarb sulfone[(2-methyl-2-methylsulfonylpropylidene)amino] N-methylcarbamate2-methyl-2-(methylsulfonyl)propanal O-[(methylamino)carbonyl]oximeSCHEMBL3500526(1E)-2-Methyl-1-(([(methylamino)carbonyl]oxy)imino)-2-(methylsulfonyl)propane #Carbamic acid, methyl-, O-[[2-methyl-2-(methylsulfonyl)propylidene]amino] deriv.Aldicarb-sulfone 1000 microg/mL in AcetoneAldicarb-sulfone 100 microg/mL in Acetonitrile
Show more names
ALDOXYCARBALDICARB-SULFONE PESTANALUCESent4.9StandakSTANDOKUC21865SulfocarbSTANDAK(R)aldoxycarbe
[(2-methyl-2-methylsulfonyl-propylidene)amino] N-methylcarbamate2-methyl-2-(methylsulfonyl) propionaldehyde O-(methylcarbamoyl) oxime7,7-Dimethyl-8,8-dioxo-4-oxa-8lambda~6~-thia-2,5-diazanon-5-en-3-one

Database identifiers

CAS
1646-88-4
PubChem CID
15438
DTXSID
DTXSID6023862
EC Number
216-710-0

Properties

Computed structural properties

XLogP
-0.6
Topological polar surface area
93.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
14

Experimental & physicochemical properties

Pesticides · 4 items

Pesticide -> EPA IRIS

Pesticides -> Carbamate Insecticides

Pesticide (Aldicarb sulfone) -> USDA PDB

Pesticide degradation product

LogP-0.57
Vapor Pressure0.00009 [mmHg]
Physical Description · 2 items

Aldicarb sulfone is a white crystalline solid. Insecticide.

White solid; [CAMEO]

Collision Cross Section149.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6023862]

Physicochemical properties

Melting point
132 · 132-135 °C
Density
1.3816 · 1.3816 (rough estimate)
vapor pressure
1.2 · 1.2×10-2 Pa (25 °C)
refractive index
1.569 · 1.5690 (estimate)
storage temp.
0 · 0-6°C
solubility
DMSO (Slightly), Methanol (Slightly)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H300 (92.9%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT LabelPoison
Fire HazardsExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Hazards Summary · 1 item

Causes weight loss in acute oral studies of rats; Causes other degenerative changes to brain and effects on true cholinesterase in 13-week constant oral studies of rats; [RTECS] A metabolite of aldicarb with less potent cholinesterase inhibiting potential; [Reference #1] May cause irritation; A lachrymator and cholinesterase inhibitor; Highly toxic by ingestion, inhalation, and skin absorption; Targets the cardiovascular system, CNS, blood, heart, and eyes; [Sigma-Aldrich MSDS] See Aldicarb. See CARBAMATE INSECTICIDES.

Reactive GroupCarbamates

Safety & protection

Fire FightingExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
First AidExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Exposure Control and Personal Protection · 1 item

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

Nonfire Spill ResponseExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Personal Protective Equipment (PPE)Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Toxicology

Treatment · 1 item

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Target OrgansNervous
Health Effects · 1 item

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

Adverse EffectsOther Poison - Carbamate
Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

Aldoxycarb is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
UE2080000
ridadr
2757
Toxicity
duck,LD50,oral,33500ug/kg (33.5mg/kg),Pesticide Manual. Vol. 9, Pg. 18, 1991.
risk_code
24-26/28

Chemistry & industry

Pharmacology

Metabolism/MetabolitesThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Uses & manufacturing

Uses · 2 items

A metabolite of aldicarb; [ChemIDplus] No active pesticide product registrations in the US; [NPIRS]

Aldoxycarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Applications · 4 items

DescriptionAldoxycarb, is also called 2-mesyl-2-methylpropionaldehyde O-methylcarbamoyloxime (IUPAC), the sulfone analog of aldicarb, is also a systemic insecticide effective for control of insects (mainly sucking insect pests such as aphids, leafhoppers, etc.).

UsesAldoxycarb is a soil applied systemic oxime carbamate insecticide effective for the control of insects (mainly sucking pests such as aphids, leafhoppers, etc.), mites and nematodes on many field (cotton, maize, etc.) and vegetable crops.

UsesAldicarb Sulfone is an analog of Aldicarb (A514650) detected in agricultural products as pesticide residue.

General DescriptionWhite crystalline solid. Insecticide.

Upstream & downstream products

Suppliers62 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
江苏智芯廷科技有限公司18221391031 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
Henan Rane Chemical Co., Ltd.+86-18738066252 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]

Additional notes

DefinitionChEBI: Aldoxycarb is a sulfone.

Related reactions

4 records

Compound notes

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